3-biphenyl-4-yl-4-cyano-1,5-dimethyl-1H-pyrrole-2-carboxylic acid

ID: ALA215272

PubChem CID: 44417081

Max Phase: Preclinical

Molecular Formula: C20H16N2O2

Molecular Weight: 316.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C#N)c(-c2ccc(-c3ccccc3)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C20H16N2O2/c1-13-17(12-21)18(19(20(23)24)22(13)2)16-10-8-15(9-11-16)14-6-4-3-5-7-14/h3-11H,1-2H3,(H,23,24)

Standard InChI Key:  WFIIIBVCKSRDRH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -0.3038  -17.4853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803  -17.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517  -16.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6717  -16.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572  -16.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313  -18.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506  -17.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413  -16.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495  -18.0022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554  -15.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627  -14.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359  -15.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720  -14.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2356  -14.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596  -14.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4178  -14.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560  -15.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208  -13.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596  -12.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241  -12.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480  -12.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053  -12.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386  -13.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1564  -17.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 12  1  0
  1  6  1  0
 12 13  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
  2  3  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  3  4  1  0
 15 18  1  0
  7  9  2  0
 18 19  2  0
  4  5  2  0
 19 20  1  0
  5  1  1  0
 20 21  2  0
 10 11  3  0
 21 22  1  0
  3 10  1  0
 22 23  2  0
 23 18  1  0
  1  2  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA215272

   3-biphenyl-4-yl-4-cyano-1,5-dimethyl-1H-pyrrole-2-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.36

Molecular Weight (Monoisotopic): 316.1212

AlogP: 4.24

#Rotatable Bonds: 3

Polar Surface Area: 66.02

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 0.80

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -0.63

References

1. Zarrinmayeh H, Tromiczak E, Zimmerman DM, Rankl N, Ho KH, Dominguez E, Castaño A, Escribano A, Fernandez C, Jimenez A, Hornback WJ, Nisenbaum ES..  (2006)  A novel class of positive allosteric modulators of AMPA receptors: design, synthesis, and structure-activity relationships of 3-biphenyl-4-yl-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid, LY2059346.,  16  (19): [PMID:16872827] [10.1016/j.bmcl.2006.07.012]

Source

Source(1):

• Scientific Literature